Water → HCID 22854879, compound

HRID 1647950Notes

Reaction equation

HRID 1647950 reaction equation
[CH3:1][O:2][C:3](=[O:20])[CH:4]([C:6]1[CH:11]=[CH:10][C:9]([CH2:12][CH:13]2[CH2:17][CH2:16][CH2:15][C:14]2=[O:18])=[C:8]([Cl:19])[CH:7]=1)[CH3:5].B.[Na].O.CCCCCC>CO>[CH3:1][O:2][C:3](=[O:20])[CH:4]([C:6]1[CH:11]=[CH:10][C:9]([CH2:12][C@@H:13]2[CH2:17][CH2:16][CH2:15][C@@H:14]2[OH:18])=[C:8]([Cl:19])[CH:7]=1)[CH3:5].[CH3:1][O:2][C:3](=[O:20])[CH:4]([C:6]1[CH:11]=[CH:10][C:9]([CH2:12][C@@H:13]2[CH2:17][CH2:16][CH2:15][C@H:14]2[OH:18])=[C:8]([Cl:19])[CH:7]=1)[CH3:5]

Participants

7

Reactant 4

HCID 962WaterHCID 8058HexaneHCID 19922602HCID 19922602, compoundHCID 178418435HCID 178418435, compound

Product 2

HCID 22854877HCID 22854877, compoundYield 28%HCID 22854879HCID 22854879, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

7 g of methyl-2-[3-chloro-4-(2-oxocyclopentane-1-yl methyl)phenyl]propionate were dissolved in 40 ml of methanol and then incorporated with 0.9 g of sodium boron hydride under agitation at room temperature, agitated at room temperature for 30 minutes, incorporated with 100 ml of water and then extracted with 100 ml of ethyl acetate. The extract obtained was washed with water, dried and then freed of the solvent at a reduced pressure to obtain a mixture of trans-form and cis-form bodies. The thus obtained mixture was adsorbed onto a silica gel-packed column and then separated with ethyl acetate.hexane (1:3) to obtain 2.0 g (yield 28%) of methyl-2-[3-chloro-4-(cis-2-hydroxycyclopentane-1-yl methyl) phenyl]propionate and 3.4 g (yield 48%) of methyl-2-[3-chloro-4-(trans-2-hydroxycyclopentane-1-yl methyl) phenyl]propionate.

Workup

  1. extractionextracted with 100 ml of ethyl acetate
  2. customThe extract obtained
  3. washwas washed with water
  4. customdried
  5. customto obtain
  6. additiona mixture of trans-form and cis-form bodies
  7. customseparated with ethyl acetate

Sources & evidence

ORD record
ord-f8225fffcdfc4dff9aeebddcc51c77de
Source dataset
uspto-grants-1995_07
Patent number
US05434292

Reaction notes

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